Substituted oxindole derivatives as protein tyrosine kinase and as protein serine/threonine kinase inhibitors

US6541503B2 · kind B2 · utility

Assignee

• SmithKline Beecham Limited · US

Inventors

• Stephen Thomas Davis · Durham, US
• Scott Howard Dickerson · Chapel Hill, US
• Stephen Frye · Durham, US
• Philip Anthony Harris · Raleigh, US
• Robert Neil Hunter, III · Boston, US
• Lee Frederick Kuyper · Durham, US
• Karen Elizabeth Lackey · Durham, US
• Michael Joseph Luzzio · Noank, US
• James Marvin Veal · Apex, US
• Duncan Walker · Boulder, US

Key dates

• Filing date: Aug 8, 2001
• Grant date: Apr 1, 2003
• Expiry date: Aug 8, 2021

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D513/04
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Compounds of formula (I): wherein X is N, CH, CCF3, or C(C1-12 aliphatic); R4 is sulfonic acid, C1-12 aliphatic-sulfonyl, sulfonyl-C1-12 aliphatic, C1-12 aliphatic-sulfonyl-C1-6 aliphatic, C1-6 aliphatic-amino, R7-sulfonyl, R7 sulfonyl-C1-12 aliphatic, R7-aminosulfonyl, R7-aminosulfonyl-C1-12 aliphatic, R7-sulfonylamino, R7-sulfonylamino-C1-12 aliphatic, aminosulfonylamino, di-C1-12 aliphatic amino, di-C1-12 aliphatic aminocarbonyl, di-C1-12 aliphatic aminosulfonyl, di-C1-12 aliphatic amino, di-C1-12 aliphatic aminocarbonyl, di-C1-12 aliphatic aminosulfonyl-C1-12 aliphatic, (R8)1-3-Arylamino, (R8)1-3-Arylsulfonyl, (R8)1-3-Aryl-aminosulfonyl, (R8)1-3-Aryl-sulfonylamino, Het-amino, Het-sulfonyl, Het-aminosulfonyl, aminoiminoamino, or aminoiminoaminosulfonyl, R5 is hydrogen; and further wherein R4 and R5 are optionally joined to form a fused ring, pharmaceutical formulations comprising them and their use in therapy, especially in the treatment of diseases mediated by CDK2 activity, such as alopecia induced by cancer chemotherapy or radiotherapy.